Greenport's expanded paid parking sparks pushback from downtown residents
Downtown residents say Greenport’s new paid-parking rules turn their own block into visitor space, just as summer signs go up and enforcement spreads.

New paid-parking signs are going up in downtown Greenport, and for year-round residents who rely on street parking near their homes, the change is already making daily life more difficult. On Main Street, Front Street and nearby blocks, neighbors say the village’s expanded system adds cost and uncertainty to the simple act of coming home, while the busiest downtown spaces are increasingly being managed for turnover instead of longtime use.
The backlash sharpened after the Village Board met on May 28 and then spilled into a private Facebook group when Trustee Mary Bess Phillips posted a timeline of the parking program. Residents argued that the village was treating them like visitors in their own neighborhood, even as officials framed the policy as a practical response to congestion and a way to help pay for road and sidewalk repairs. The tension cuts to a central Greenport question: whether the village’s tourism economy is getting priority over the people who live there full time.

Village materials show the parking push did not appear overnight. In 2022, the board said its purpose was to address a shortage of parking in Greenport and to amend off-street parking rules to benefit residents, guests, workers, visitors, businesses and institutions. The village’s earlier 45-day paid-parking trial on Main and Front streets in September 2024 was part of a larger study of parking and traffic management, and no citations were issued during the test. Mayor Kevin Stuessi said then that the village wanted to assess whether drivers would accept the system before enforcement began, with a larger rollout planned for peak summer months the following year.
That rollout is now landing on the village’s core downtown parking supply. Greenport’s parking FAQ says timed parking is enforced on Front Street, Main Street, First Street and designated spots in the IGA parking lot, extending the policy beyond a single municipal lot and into the heart of the village. The board roster now includes Mayor Patrick Brennan, Deputy Mayor Mary Bess Phillips, Trustees Lily Dougherty-Johnson and Julia Robins, and Trustee Kevin Stuessi, all of whom are dealing with the practical politics of parking in a summer village that depends on visitors but is also home to residents who park on the street every night.
Greenport’s move also reflects a broader East End shift. Sag Harbor has already collected $250,000 from paid parking since 2021, with less than 1% coming from the 11963 ZIP code, a number that has become a warning sign for communities weighing who really pays for downtown access. East Hampton Town, East Hampton Village and Montauk have all expanded paid parking as well, making Greenport’s fight part of a larger regional debate over whether parking policy is being used to fund infrastructure or to quietly reshape who downtown is for.
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